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Antidepressant
Triazoledione
Другие языки:

Triazoledione

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Triazoledione
Triazoledione.svg
Clinical data
Other names BMS-180492
Pharmacokinetic data
Elimination half-life 18 hours
Identifiers
  • 1-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-4-(2-phenoxyethyl)-1,2,4-triazolidine-3,5-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C23H28ClN5O3
Molar mass 457.96 g·mol−1
3D model (JSmol)
  • C1CN(CCN1CCCN2C(=O)N(C(=O)N2)CCOC3=CC=CC=C3)C4=CC(=CC=C4)Cl
  • InChI=1S/C23H28ClN5O3/c24-19-6-4-7-20(18-19)27-14-12-26(13-15-27)10-5-11-29-23(31)28(22(30)25-29)16-17-32-21-8-2-1-3-9-21/h1-4,6-9,18H,5,10-17H2,(H,25,30)
  • Key:BTNXVMLCKOPOEP-UHFFFAOYSA-N

Triazoledione (developmental code name BMS-180492) is a phenylpiperazine compound and a major metabolite of the antidepressant nefazodone. It is active, but with substantially reduced potency compared to nefazodone (approximately one-seventh). As such, it has been suggested that it is unlikely that triazoledione contributes significantly to the pharmacology of nefazodone. However, triazoledione may reach concentrations as great as 10 times those of nefazodone, and hence could still be a significant contributor to its therapeutic effects.

Pharmacology

Triazoledione
Site Ki (nM) Species Ref
SERT ≥34,527
≥26,471		 Human
Rat
NET >100,000
100,000		 Human
Rat
DAT ND ND ND
5-HT1A 636–1,371 Rat
5-HT2A 159–211 Rat
5-HT2C ND ND ND
α1 173
1,000		 Human
Rat
α2 1,915
1,000		 Human
Rat
β >100,000 Rat
H1 11 Guinea pig
mACh >100,000 Rat
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Triazoledione shows significant affinity for the serotonin 5-HT1A and 5-HT2A receptors, the α1-adrenergic receptor, and the histamine H1 receptor. It shows negligible affinity for the serotonin and norepinephrine transporters and the muscarinic acetylcholine receptors.

Comparison of binding profiles of triazoledione and related compounds
Compound 5-HT1A 5-HT2A SERT NET α1 α2 β H1 mACh
Hydroxynefazodone 56–589 7.2–34 165–1,203 376–1,053 8.0–145 63–2,490 >1,000 28 11,357
mCPP 16–411 110–433 127–432 490–4,360 97–763 112–371 4,890 449 4,702
Nefazodone 52–1,030 7.1–32 181–549 200–713 5.5–144 84–41,700 >100,000 30 4,569
Trazodone 42–288 11–20 115–690 ≥20,887 12–23 106–1,070 47,100 29 12,188
Triazoledione 636–1,371 159–211 ≥26,471 >100,000 ≥173 ≥1,915 >100,000 11 >100,000
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

See also




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